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Search results; Over 1,000 homes in Old Saybrook

Guest favourite
Cottage in Old Saybrook
Luxury Driftwood Cottage @ Saybrook Point
3 bedrooms, 3 beds, 2 private bathrooms
7–13 Sept
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4.9 out of 5 average rating, 67 reviews
Superhost
Home in Old Saybrook
Cozy beach side home Chalker Beach Old Saybrook
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 23 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
27 Aug – 1 Sept
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Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 bathrooms
26–31 Aug
5.0 out of 5 average rating, 101 reviews
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Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
4.75 out of 5 average rating, 254 reviews
Guest favourite
Home in Old Saybrook
Red Bird Waterfront Home. Dock available extra!
3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.94 out of 5 average rating, 36 reviews
Guest favourite
Home in Old Saybrook
Steps to Beach! *Cozy Cottage* Pet Friendly
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
4.92 out of 5 average rating, 104 reviews
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Home in Old Saybrook
Year Round Beach House in Old Saybrook, CT.- Pets
4 bedrooms, 7 beds, 2 bathrooms
8–13 Sept
4.97 out of 5 average rating, 145 reviews
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Cottage in Old Saybrook
Beautiful View Cottage
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 165 reviews
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Cottage in Old Saybrook
Osprey Cozy Cottage | Near Downtown & Beaches
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 14 reviews
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Home in Old Saybrook
Water Views and Walk to Beach
4 bedrooms, 4 beds, 3.5 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 66 reviews
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Cabin in Colchester
The Colchester Cottage
1 bedroom, 3 beds, 1 bathroom
23–28 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Cottage in Old Saybrook
Charming Old Saybrook Cottage < 1 Mi to Beach
4 bedrooms, 4 beds, 2 bathrooms
16–21 Oct
4.87 out of 5 average rating, 39 reviews
Home in Westbrook
Luxe 5,600-Sq-Ft Estate Waterfront + Pool
5 bedrooms, 8 beds, 5.5 bathrooms
7–12 Sept
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Guest suite in Old Saybrook
Cozy Loft Getaway
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 110 reviews
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Home in Old Saybrook
Best of both worlds!
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
4.92 out of 5 average rating, 113 reviews
Guest favourite
Home in Old Saybrook
Summertime in Old Saybrook on the Oyster River
5 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Bungalow in Westbrook
Adorable single story cottage-by-the-sea
2 bedrooms, 2 queen beds, WC
15–20 Sept
4.87 out of 5 average rating, 54 reviews